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251003

Sigma-Aldrich

2-Bromo-3-methylbutyric acid

97%

Synonym(s):

α-Bromoisovaleric acid, 2-Bromoisovaleric acid

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About This Item

Linear Formula:
(CH3)2CHCHBrCOOH
CAS Number:
565-74-2
Molecular Weight:
181.03
Beilstein:
1721146
EC Number:
209-291-0
MDL number:
MFCD00004210
UNSPSC Code:
12352100
PubChem Substance ID:
24855092
NACRES:
NA.22

Assay

97%

form

solid

bp

124-126 °C/20 mmHg (lit.)

mp

39-42 °C (lit.)

solubility

alcohol: soluble(lit.)
diethyl ether: soluble(lit.)
water: very slightly soluble(lit.)

SMILES string

CC(C)C(Br)C(O)=O

InChI

1S/C5H9BrO2/c1-3(2)4(6)5(7)8/h3-4H,1-2H3,(H,7,8)

InChI key

UEBARDWJXBGYEJ-UHFFFAOYSA-N

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General description

Mechanism of action of methylamine on optically active 2-bromo-3-methylbutyric acid has been investigated.

Application

2-Bromo-3-methylbutyric acid has been used in the preparation of optically active N-methylvalines.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302 + H312,H314

Hazard Classifications

Acute Tox. 4 Oral - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

224.6 °F - closed cup

Flash Point(C)

107 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Depsipeptides.
Ovchinnikov YA, et al.
Russian Chemical Bulletin, 11(11), 1955-1961 (1962)
M Polhuijs et al.
Biochemical pharmacology, 44(7), 1249-1253 (1992-10-06)
Glutathione (GSH) conjugation of the separate enantiomers of five 2-bromocarboxylic acids and some of their urea derivatives by rat liver GSH transferases (GSTs) was studied. The liver cytosolic fraction conjugated all compounds, except for (R)-2-bromoisovaleric acid, with a variable degree
M Polhuijs et al.
Biochemical pharmacology, 38(22), 3957-3962 (1989-11-15)
The glutathione (GSH) conjugation of (R)-and (S)-alpha-bromoisovaleric acid (BI) in the rat in vivo, and its stereoselectivity, have been characterized. After administration of racemic [1-14C]BI two radioactive metabolites were found in bile: only one of the possible diastereomeric BI-GSH conjugates
J M Te Koppele et al.
The Biochemical journal, 252(1), 137-142 (1988-05-15)
The stereoselectivity of purified rat GSH transferases towards alpha-bromoisovaleric acid (BI) and its amide derivative alpha-bromoisovalerylurea (BIU) was investigated. GSH transferase 2-2 was the only enzyme to catalyse the conjugation of BI and was selective for the (S)-enantiomer. The conjugation

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